Enzyme inhibition and antibacterial potential of 4-Hydroxycoumarin derivatives

Afia Saleem,Sidra Khan,Majid Ali,Asma Khan,Umar Farooq,Syed Majid Bukhari,Asma Zaidi,Farhan Ahmed Khan,Adeem Mahmood,Kausar Hussain Shah

doi:10.1590/s2175-97902019000418654

Abstract

The 4-Hydroxycoumarin derivatives are known to show a broad spectrum of pharmacological applications. In this paper we are reporting the synthesis of a new series of 4-Hydroxycoumarin derivatives synthesized through Knovenegal condensation; they were characterized by using UV-Vis, FT-IR, NMR spectroscopies. The synthesized compounds were evaluated for antibacterial activity against Staphylococcus aureus and Salmonella typhimurium strains. The compounds (2), (3) and (8) showed favorable antibacterial activity with zone of inhibitions 26.5± 0.84, 26.0 ± 0.56 and 26.0 ± 0.26 against Staphylococcus aureus (Gram-positive) respectively. However, the compounds (5) and (9) were found more active with 19.5 ± 0.59 and 19.5 ± 0.32 zone of inhibitions against Salmonella typhimurium (Gram-negative). Whereas, in urease inhibition assay, none of the synthesized derivatives showed significant anti-urease activity; although, in carbonic anhydrase-II inhibition assay, the compound (2) and (6) showed enzyme inhibition activity with IC50 values 263±0.3 and 456±0.1, respectively.

Highlights

In this paper, we are reporting new derivatives of 4-Hydroxycoumarin which are synthesized through Knovenegal condensation
The presence of nitrogen containing functional group has been confirmed by the appearance of signals in FT-IR at 1340 cm-1 and 1524 cm-1. This confirms that a successful nitrogen containing coumarin has been synthesized
The possibility of nitration occurring at alkene functionality has been ruled out by the presence of stretching vibration of the alkene group at 1608 cm-1 which verifies that the alkene functionality is intact in the synthesized molecule

Summary

Introduction

The derivatives of 4-Hydroxycoumarin (Figure 1) are of great interest due to their broad spectrum of pharmacological activities including antioxidant (Jung, Park, 2009), anti-allergy (Lee et al, 2004), antiviral (Yu et al, 2003), anti-diabetic (Kontogiorgis, HadjipavlouLitina, 2005), anti-HIV (Tosun et al, 2008), anticonvulsant (Sashidhara et al, 2010), anti-tubercular (Jin, Chen, Zhu, 2007), anti-hyperlipidmeic (Hamdi et al, 2011), rodenticidal (Khan et al, 2004) and antifungal (Gao et al, 2010). The organic compounds such as 4-Hydroxycoumarin having active methylene group can undergo Knovenegal condensation with compounds possessing carbonyl functionality (Kidwai et al, 2007). In this paper, we are reporting new derivatives of 4-Hydroxycoumarin which are synthesized through Knovenegal condensation

Methods

Results

Conclusion